1. Field of Invention
This invention relates to 2-substituted-1-naphthols, and processes for their preparation, pharmaceutical compositions containing them and pharmaceutical methods using them.
2. Prior Art
U.S. Pat. No. 3,998,966 issued Dec. 21, 1976 to Fried and Harrison discloses 6-substituted 2-naphthyl acetic acid derivatives with antiinflammatory. analgesic, antipyretic and antipruritic activity.
U.S. Pat. No. 3,969,415 issued July 13, 1976 to E. G. Galantay discloses antiinflammatory 1-(2-naphthyl)-2,3-butandien-1-ols of the formula ##STR1## wherein R is H, Fl, Cl, Br, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 -alkylthio or difluoromethoxy, R.sup.1 is H or C.sub.1 -C.sub.4 alkyl, R.sup.2 is H or CH.sub.3 and R.sup.3 and R.sup.4 are independently H or C.sub.1 -C.sub.4 alkyl provided that at least one of R.sup.3 and R.sup.4 is H when R.sup.2 is CH.sub.3.
U.S. Pat. No. 4,442,392 issued Jan. 17, 1984 to A. C. Goudie discloses antiinflammatory naphthyl compounds of the formula ##STR2## wherein R.sup.1 is chloro or methoxy and R.sup.2 is methyl, ethyl, benzyl, 2-methoxyethyl, phenyl, 4-methoxyphenyl or aminomethyl.
European Patent Application No. 0082005 filed Dec. 13, 1982 by Nelson et al., discloses antiinflammatory naphthoxyalkylamines of the formula ##STR3## wherein y is halo. alkoxy, or alkyl; a is 0 or 1; b is an integer from 2-12 with the proviso that if b is 2 or 3, a cannot be 0; and x is selected from --OH. OR.sup.1, NH.sub.2, NHR.sup.1, NR.sub.1.sup.2, ##STR4## and --NHCONHR.sup.2 in which each R.sup.1 is independently alkyl or phenyl or in --NR.sub.2.sup.1, both R.sup.1 together are alkylene; and R.sup.2 is cycloalkyl or phenyl.
European Patent Application No. 0036502 filed Feb. 25, 1981 by G. Wurm discloses naphthoquinones of the formula ##STR5## wherein R is methyl, ethyl, propyl, isopropyl, or tertiary butyl. These compounds are disclosed as prostaglandin synthetase inhibitors, useful in the treatment of allergy and anaphylactic shock.
European patent Application No. 0127726 filed Jan. 27, 1984 by Slapke et al., discloses aromatic hydroxamic acid derivatives as 5-lipoxygenase inhibitors useful in the treatment of asthma. Included is the compound having the formula ##STR6##
U.K. Patent No. 2055097 issued Feb. 25, 1981 to Terao et al. discloses quinone derivatives of the formula ##STR7## wherein .alpha.-.beta. means a saturated bond or double bond; each R independently of one another is a methyl or methoxy group, or two R's taken together repersent a --CH.dbd.CH--CH.dbd.CH-- group; n is 0-9; R.sup.2 is H or OH when .alpha.-.beta. is saturated, R.sup.2 is H when .alpha.-.beta. is a double bond; when .alpha.-.beta. is a double bond or when R.sup.2 is OH, R.sup.1 is COOH, a --(CH.sub.2).sub.m OH group or ##STR8## when .alpha.-.beta. is a saturated bond and R.sub.2 is H, R.sup.1 is hydroxymethyl or ##STR9## m=1 to 3. These compounds are active as bronchodilators useful in the treatment of asthma.
G. Xi et al. in Yaoxue Xuebao 15, 548 (1980) discloses the synthesis of antiasthmatic quinones of the formula ##STR10## where n=4-8. A number of alkyl naphthols are disclosed as intermediates.
A number of references disclose 1-naphthol as a lipoxygenase inhibitor, including T. Nakadate et al., Gann, 75, 214 (1984); J. Van Wauwe and J. Goossens, Prostaglandins. 26, 725 (1983); and R. V. Panganamala et al.. Prostaglandins, 14, 261 (1977).
M. Shiraishi and S. Tereo in J. Chem. Soc. Perkin Trans. I, 1591 (1983) disclose ethylenic and acetylenic quinones which inhibit 5-lipoxygenase.
A number of references disclose 2-alkyl-1-naphthols as intermediates in the preparation of other chemical compounds including N. S. Narasimhan and R. S. Mali. Tetrahedron, 31, 1005 (1975); Newman et al., J. Org. Chem, 43, 524 (1978); B. Miller and W. Lin. J. Org. Chem. 43. 4441 (1978); K. A. parker and J. L. Kallmerton, Tetrahedron Letters, 14, 1197 (1979); D. W. Cameron et al., Aust J. Chem. 35. 1481 (1982); P. Barua et al., Chem Ind. 303 (1984); T. Kometani et al., J. Org. Chem. 48, 2630 (1983); T. Zhong and M. Huang, Hua Hseuh Hseuh Pao, 39, 229 (1981); C. Pac et al., Synthesis, 589 (1978); I. A. Akhtar and J. J. McCullough in J. Org. Chem., 46, 1447 (1981); R. Alonso Cermona et al., An. Quim.. Ser. C. 78, 9 (1982); I. M. Andreeva et al., Khim. Geterotsikl. Soedin. 2, 181 (1983); D. Berney and K. Schuh, Helv. Chim. Acta, 62, 1268 (1979); S. P. Starkov, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 20, 1099 (1977); M. R. Saidi. Indian J. Chem. 474 (1982); L. Z. Oblasova and G. D. Kharlampovich. Khim. Pro-St. (Moscow), 10, 776 (1977); F. T. Sher and G. A. Berchtold. J. Org. Chem. 42. 2569 (1977); M. Mully et al., Helv. Chim. Acta. 58, 610 (1975); T. R. Kasturi and R. Sivaramakrishnan, Proc. Indian Acad. Sci., 86, 309 (1977) and T. Hirashima et., in Japanese Patent No. 7010339 issued Apr. 14. 1970.
A number of references disclose 2-benzyl-1-naphthol as a chemical entity, such as B. Miller and W. Lin, J. Org. Chem., 44, 887 (1979) and Z. Aizenshtat et al., J. Org. Chem., 42, 2386 (1977).